High performance liquid chromatography in the quantitative analysis of hydroxycinnamic acids in plants growing in the Russian Federation
Abstract
Currently, high performance liquid chromatography method has a leading position in drug quality control and study of plant material. In recent years, a large amount of information on the study of plants growing or cultivated on the territory of the Russian Federation for the identification of hydroxycinnamic acids has been accumulated. The purpose of this review is systematization of information on the use of high performance liquid chromatography method for the determination of the quantitative content of hydroxycinnamic acids in plants growing or cultivated on the territory of the Russian Federation. The systematization of scientific research published in scientific journals and abstracts of conferences performed in the Russian Federation was performed. The analysis of these studies showed that Russian scientists over the past 15 years started widely use the HPLC method for the determination of the quantitative content of hydroxycinnamic acids in plant material. Almost all studies were performed using foreign equipment, and mobile phases of solvents were successfully used in the analysis for both isocratic and gradient elution modes. The results of the search of hydroxycinnamic acids in plant raw material of about 150 plant species were published 50 literature sources. Grass or leaves of plants were mainly used as raw material, and chlorogenic acid was found in almost all the plants studied. The highest amount of chlorogenic acid was find in fruits of some Berberis species, leaves ofParasenecio hasstatus (L.) H. Koyama, Nepeta cataria L. leaves , Galeopsis bifida L. grass , Cynara cardunculus L. leaves. Plants containing rosmarinic acid – Prunella vulgaris L., Prunella laciniata (L.) L., Majorana hortensis, Mentha spicata L., Artemisia santonica, Origanum vulgare and plants containing caffeic acid - Arctium tomentosum Mill. leaves are also promising. In the gradient elution mode, the content of hydroxycinnamic acids in Prunella vulgaris L., P. laciniata (L.) L. and P. grandiflora (L.) Turra. was determined. At the same time, the proportion of solution B (a mixture of acetonitrile - methanol - water with perchloric acid in a ratio of 40:40:20, pH 2.5) in a mixture with solution A (an aqueous solution of perchloric acid, pH 1.8) increased from 0% to 100% during 80 minutes at 30°C. Caffeic acid (traces) and rosmarinic acid (up to 2.9%) were found [33].
These plants can serve as potential sources for the creation of new highly effective drugs. However, for this purpose it is necessary to have data on the dynamics of accumulation of hydroxycinnamic acids depending on the season, place of growth, terms and conditions of harvesting, storage of the plant. In the absence of such data, studies aimed at normalization of the amount of hydroxycinnamic acids in potential plant raw material with high content are required.
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References
Sychev K.S. Unifikacija uslovij kontrolja prirodnyh organicheskih soedinenij v rezhime obrashhenno-fazovoj zhidkostnoj hromatografii. Chast' 1. Flavonoly, flavonol-glikozidy, katehiny, gidroksikorichnye kisloty. Fundamental'nye i prikladnye problemy tehniki i tehnologii. 2019; 1(291): 120-127. (In Russ.)
Marahova, A.I. Fiziko-himicheskij analiz fenol'nyh soedinenij lekarstvennogo rastitel'nogo syr'ja. Farmacija. 2009; 3: 52-55. (In Russ.)
Gosudarstvennaja farmakopeja Rossijskoj Federacii: IV tom. MZ RF. 14-e izd. M.: Medicina. 2018, 7019 p. – Rezhim dostupa: http://femb.ru/femb/pharmacopea.php . (In Russ.)
Kurkin V.A. Fenilpropanoidy kak vazhnejshaja gruppa biologicheski aktivnyh soedinenij lekarstvennyh rastenij. Mezhdunarodnyj zhurnal prikladnyh i fundamental'nyh issledovani. 2015; 12-7: 1338-1342. URL: https://applied-research.ru/ru/article/view?id=8148 (data obrashhenija: 21.05.2022). (In Russ.)
Mathew S., Abraham T.E. Ferulic acid: an antioxidant found naturally in plant cell walls and feruloyl esterases involved in its release and their applications. Critical Reviews in Biotechnology, 2000; 24(2/3): 59-83.
Sajbel' O.L., Baslinov S.L., Dargaeva T.D. Nakoplenie cikorievoj kisloty v nadzemnoj chasti dikorastushhego cikorija obyknovennogo (Cichorium intybus L.). «Perspektivy lekarstvennogo rastenievedenija», sbornik trudov mezhdunarodnoj nauchnoj konferencii M. VILAR, 2018; 533-539. (In Russ.)
Chuklin R.E., Maslikova G.V. Klinicheskaja farmakologija kofejnoj kisloty. Mezhdunarodnyj zhurnal jeksperimental'nogo obrazovanija. 2016; 12-3: 436-437. Rezhim dostupa: URL: https://expeducation.ru/ru/article/view?id=11018 (data obrashhenija: 08.06.2022). (In Russ.)
Azarova O.V., Brjuhanov V.M., Zverev Ja.F. Farmakologicheskaja aktivnost' rozmarinovoj kisloty. Voprosy biologicheskoj, medicinskoj i farmacevticheskoj himii. 2010; 6: 28-33. (In Russ.)
Dejneka V.I., Olejnic E.Ju., Dejneka L.A. Hromatograficheskoe povedenie monokofeoilhinnyh i dikofeoilhinnyh kislot v uslovijah OF VJeZhH:zavisimost' ot stroenija. Sorbtsionnye i khromatograficheskie protsessy. 2021; 21(4): 458-465. https://doi.org/10.17308/sorpchrom.2021.21/3628 (In Russ.)
Shplis O.N., Kolomiec N.Je., Abramec N.Ju., Karakchieva N.I., Bondarchuk R.A., Zhalnina L.V. Fenol'nye soedinenija ljadvenca rogatogo kul'tiviruemogo v Zapadnoj Sibiri. «Rol' metabolomiki v sovershenstvovanii biotehnologicheskih sredstv proizvodstva», sbornik trudov II mezhdunarodnoj nauchnoj konferencii. M. 2019. 228-232. (In Russ.)
Mirovich V.M., Olennikov D.N., Petuhova S.A., Posohina A.A. Flavonoidy i fenilpropanoidy nadzemnyh organov volodushki mnogozhilkovoj (Bupleurum multinerve DC.) flory Pribajkal'ja. Himija rastitel'nogo syr'ja. 2020; 4: 121-128. (In Russ.)
Tohsirova Z.M., Popov I.V., Popova O.I. Issledovanie fenol'nyh soedinenij list'ev i pobegov rozmarina lekarstvennogo (Rosmarinus officinalis L.), introducirovannogo v botanicheskom sadu Pjatigorskogo mediko-farmacevticheskogo instituta. Himija rastitel'nogo syr'j, 2018; 3; 199-207. https://doi.org/10.14258/jcprm.2018033733 (In Russ.)
Velichko V.V., Hanina M.A., Rodin A.P. Rezul'taty farmakognosticheskogo issledovanija list'ev i kornej lopuha vojlochnogo. Vestnik Moskovskogo gosudarstvennogo oblastnogo gumanitarnogo instituta. Serija: mediko-biologicheskie nauki. 2014; 1(1): 16-20. (In Russ.)
Belova E.A., Tritjek V.S., Shul'gau Z.T., Guljaev A.E., Kovalenko L.V., Drenin A.A., Botirov Je.H. Fenol'nye soedinenija jagod treh vidov rastenij roda Vaccinium L. «Fenol'nye soedinenija: svojstva, aktivnost', innovacii», sbornik nauchnyh statej po materialam X Mezhdunarodnogo simpoziuma «Fenol'nye soedinenija: fundamental'nye i prikladnye aspekty». Moskva, 14-19 maja 2018, 227-235. (In Russ.)
Alekseeva L.I., Teterjuk L.V. Fenol'nye soedinenija Thymus talijevii Klok. Et Schost. Himija rastitel'nogo syr'ja. 2008; 4: 65-68. (In Russ.)
Dejneka V.I., Hlebnikov V.A., Sorokopudov V.N., Anisimovich I.P. Hlorogenovaja kislota plodov i list'ev nekotoryh rastenij semejstva Berberidaceae. Himija rastitel'nogo syr'ja, 2008; 1: 57-61. (In Russ.)
Lukashov R.I. Vlijanie prirody i ob#emnoj doli rastvoritelej na jekstrakciju gidroksikorichnyh kislot iz travy jehinacei purpurnoj. «Sovremennye problemy farmakognozii», sbornik materialov III Mezhvuzovskoj nauchno-prakticheskoj konferencii s mezhdunarodnym uchastiem, posvjashhennoj 100-letiju Samarskogo gosudarstvennogo medicinskogo universiteta. 27 oktjabrja 2018. Samara, 84-89. (In Russ.)
Bubenchikova V.N., Nikitin E.A., Kulik O.N. Izuchenie fenol'nyh soedinenij travy kolokol'chika kruglolistnogo (Campanula rotundifolia) metodom VJeZhH–MSD. «Fenol'nye soedinenija: svojstva, aktivnost', innovacii», sbornik nauchnyh statej po materialam X Mezhdunarodnogo simpoziuma «Fenol'nye soedinenija: fundamental'nye i prikladnye aspekty», Moskva, 14-19 maja 2018; 246-253. (In Russ.)
Krasjuk E.V., Pupykina K.A., Anishhenko I.E. Harakteristika fenol'nyh soedinenij vidov monardy, introducirovannyh v Respublike Bashkortostan. Bashkirskij himicheskij zhurnal; 2015; 22(3): 79-83. (In Russ.)
Pelivanova S.L., Selina I.I., Andreeva O.A., Oganesjan Je.T. Polifenol'nyj sostav list'ev kryzhovnika otklonennogo i shelkovicy chernoj. Nauchnye vedomosti. Serija Medicina . Farmacija. 2012; 22(20/1): 170-173. (In Russ.)
Kopyt'ko Ja.F., Dargaeva T.D. Issledovanie sostava fenol'nyh veshhestv travy Knautia arvensis metodom VJeZhH. «Fenol'nye soedinenija: svojstva, aktivnost', innovacii», sbornik nauchnyh statej po materialam X Mezhdunarodnogo simpoziuma «Fenol'nye soedinenija: fundamental'nye i prikladnye aspekty», Moskva, 14-19 maja 2018, 303-306. (In Russ.)
Bombello T.V., Petrichenko V.V., Krotkova V.A. Fenol'nye soedinenija nekotoryh vidov roda ochanka (Euphrasia L.) flory Permskogo kraja. Himija rastitel'nogo syr'j. 2011; 4: 177-180. (In Russ.)
Kashhenko N.I., Olennikov D.N. Himicheskij profil' i biologicheskaja aktivnost' flavonoidov i fenilpropanoidov Nepeta cataria L. (Lamiaceae), introducirovannogo v Vostochnoj Sibiri, Himija rastitel'nogo syr'ja. 2011; 2: 25-32. (In Russ.)
Chirikova N.K., Olennikov D.N. Hemoraznoobrazie i biologicheskaja aktivnost' sinantropnyh rastenij Sibiri. I. Galeopsis bifida BOENN. (Lamiaceae). Himija rastitel'nogo syr'ja. 2016; 2: 33-46. (In Russ.)
Olennikov D.N., Chirikova N.K., Cyrenzhapov A.V. Fenilpropanoidy Parasenecio hastatus (Compositae) i ih ranozazhivljajushhaja aktivnost'. Himija rastitel'nogo syr'ja, 2020; 1: 97-105. https://doi.org/10.14258/jcpim.2020015223(In Russ.)
Grebennikova O.A., Palij A.E., Hlypenko L.A., Rabotjagov V.D. Biologicheski aktivnye veshhestva Hyssopus officinalis L. Orbital'. 2017; 1; 21-28. (In Russ.)
Bazarnova Ju.G., Ivanchenko O.B. Issledovanie sostava biologicheski aktivnyh veshhestv jekstraktov dikorastushhih rastenij. Voprosy pitanija. 2016; 85(5): 100-107. (In Russ.)
Plugatar' Ju.V., Shevchuk O.M., Logvinenko L.A., Lejba V.D., Palij I.N. Soderzhanie fenol'nyh soedinenij v nadzemnoj masse Prunella vulgaris L. po gradientu vysoty nad urovnem morja. Bjulleten' Gosudarstvennogo Nikitskogo botanicheskogo sad. 2017; 125: 42-46. (In Russ.)
Kutakova N.A., Morozkova I.A., Vasil'eva N.N., Bashkina I.E., Aleksandrova Ju.V. Fenol'nye soedinenija plodov barbarisa i shipovnika. Izvestija vysshih uchebnyh zavedenij. Lesnoj zhurnal. 2019; 5 (371): 115-124. https://doi.org/10.17238/issn0536-1036.2019.5.115 (In Russ.)
Starceva O.V., Palij I.N., Simagina N.O., Makaricheva A.A. Bystryj metod polukolichestvennogo opredelenija hlorogenovoj kisloty i ejo proizvodnyh v polyni. Orbital'. 2017; 1: 7-13. (In Russ.)
. Perova I. B., Zhogova A.A., Cherkashin A. V., Jeller K.I., Ramenskaja G.V., Samylina I.A. Biologicheski aktivnye veshhestva plodov kaliny obyknovennoj. Himiko- farmacevticheskij zhurnal. 2014; 48(5): 32-39. (In Russ.)
Sajbel' O.L., Dargaeva T.D., Cicilin A.N., Dul V.N. Razrabotka metodiki kolichestvennogo analiza biologicheski aktivnyh veshhestv i ocenka dinamiki ih nakoplenija v zavisimosti ot fazy vegetacii cikorija obyknovennogo (Cichorium intybus L.). Voprosy biologicheskoj, medicinskoj i farmacevticheskoj himii. 2016; 6: 20-24. (In Russ.)
Shamilov A.A., Popova N.V., Ivashev M.N. Poisk istochnikov rozmarinovoj kisloty vo flore Severnogo Kavkaza. Sovremennye problemy nauki i obrazovanija, 2014; 4, Rezhim dostupa: URL: http://science-education.ru/ru/article/view?id=14138 (data obrashhenija: 19.05.2020 (In Russ.)
Dejneka V.I., Tret'jakov M.Yu., Olejnic E.Yu., Pavlov A.A., Dejneka L.A., Blinova I.P., Manohina L.A. Opredelenie antocianov i hlorogenovyh kislot v plodah rastenij roda Aronija: Opyt hemosistematiki. Himija rastitel'nogo syr'ja. 2018; 2: 161-167. (In Russ.)
Vernikovskaja N.A., Temerdashev Z.A. Identifikacija i hromatograficheskoe opredelenie fenol'nyh soedinenij v tysjachelistnike obyknovennom Analitika i kontrol'. 2012; 16(2): 188-194. (In Russ.)
Petruk A.A., Vysochina G.I. Fenol'nye soedinenija Rolygonum aviculare L. (Polygonaceae) iz geograficheski otdalennyh populjacij. Izvestija vuzov. Prikladnaja himija i biotehnologij. 2019; 9(1): 95-101. https://doi.org/.org/10.21285/2227-2925-2019-9-1-95-101 (In Russ.)
Palij A.E., Grebennikova O.A., Rabotjagov V.D., Palij I.N. Biologicheski aktivnye veshhestva prjano-aromaticheskih i lekarstvennyh rastenij kollekcii Nikitskogo botanicheskogo sada. «Biologija rastenij i sadovodstvo: teorija, innovacii», sbornik nauchnyh trudov GNBS. 2014; 139: 107-115. (In Russ.)
Denisenko Yu.O., Andreeva I.N., Denisenko O.N., Fedorova E.P., Chelova L.V. Vlijanie sposoba poluchenija jekstrakcionnyh preparatov iz travy jehinacei purpurnoj na sostav gidroksikorichnyh kislot. Sovremennye problemy nauki i obrazovanija. 2011; 6. Rezhim dospupa: URL: http://science-education.ru/ru/article/view?id=5281 (data obrashhenija: 23.05.2021). (In Russ.)
Pankratova G.A., Almakaeva N.I., Semenova E.V., Mel'nikov O.M., Tihonova E.V. Soderzhanie gidroksikorichnyh kislot v list'jah razlichnyh sortov Cynara cardunculus L. «Novye dostizhenija v himii i himicheskoj tehnologii rastitel'nogo syr'ja», sbornik nauchnyh trudov. Barnaul, 24-28 aprelja 2017, 274-276. (In Russ.)
Kopyt'ko Ja.F., Dargaeva T.D., Rendjuk T.D. Sostav travy korostavnika polevogo (Knautia arvensis L.), Himiko-farmacevticheskij zhurnal. 2020; 54(7): 41-48. https://doi.org/10.30906/0023-1134-2020-54-7-41-48 (In Russ.)
Grebennikova O.A., Palij A.E., Rabotjagov V.D. Fenol'nye soedinenija vodno-jetanol'nogo jekstrakta Mentha longifolia L.. Farmacija i farmakologija. 2014; 2(6-7): 5-7. (In Russ.)
Grebennikova O.A., Palij A.E., Hristova Yu.P. Biologicheski aktivnye veshhestva Mentha spicata L. Himija rastitel'nogo syr'ja. 2014; 4: 203-208. (In Russ.)
Zhogova A.A., Perova I. B, Samylina I.A., Jeller K.I., Ramenskaja G.V. Identifikacija i kolichestvennoe opredelenie osnovnyh biologicheski aktivnyh veshhestv travy pustyrnika s pomoshh'ju VJeZhH-mass-spektrometrii. Himiko-farmacevticheskij zhurnal. 2014; 48(7): 35-40. (In Russ.)
Kostikova, V.A., Bobokalonov K.A., Kuznecov A.A. Fenol'nye soedinenija list'ev i socvetij Spiraea baldshuanica B. Fedtsch. Izvestija vuzov. Prikladnaja himija i biotehnologija. 2021; 1(36): 53-60. (In Russ.)
Selina I.I., Andreeva O.A., Oganesjan Je.T. Izuchenie polifenol'nogo sostava list'ev shelkovicy chjornoj (Morus nigra L.). «Razrabotka, issledovanie i marketing novoj farmacevticheskoj produkcii», sbornik nauchnyh trudov.Pjatigorsk. 2013; 68: 101-102. (In Russ.)
Perova I.B., Jeller K.I., Mal'ceva A.A., Chistjakova A.S., Slivkin A.I., Sorokina A.A. Gidroksikorichnye kisloty travy gorca pochechujnogo. Farmacij. 2017; 66(5): 27-31. (In Russ.)
Palij A.E., Melikov F.M., Grebennikova O.A., Rabotjagov V.D. Rozmarinovaja kislota i ee syr'evye istochniki v Krymu. Farmacija i farmakologija. 2015; 9(2): 7-12. (In Russ.)
Moiseev D.V., Stojakova I.I. Opredelenie fenol'nyh kislot v trave melissy lekarstvennoj metodom VJeZhH. «Razrabotka, issledovanie i marketing novoj farmacevticheskoj produkcii», sbornik nauchnyh trudov. Izhevsk. 2019; 74: 32-33. (In Russ.)
Caniova A., Brandsteterova E. HPLC analysis of phenolic acids in Melissa officinalis. J. Liq. Chrom. & Rel. Technol. 2001; 24(17): 2647-2659.
Medvedev Ju.V., Perederjaev O.I., Arzamascev A.P., Jeller K.I., Prokof'eva V.I. Opredelenie gidroksikorichnyh kislot v lekarstvennom rastitel'nom syr'e i ob#ektah rastitel'nogo proishozhdenija. Voprosy biologicheskoj, medicinskoj i farmacevticheskoj himii. 2010; 3: 25-31. (In Russ.)